4-Methylmorpholine → (4aR,7aS)-1-[(4-fluorophenyl)methyl]-4-hydroxy-3-(7-iodo-1,1-dioxo-4H-1$l^{6},2,4-benzothiadiazin-3-yl)-5,6,7,7a-tetrahydro-4aH-cyclopenta[b]pyridin-2-one

HRID 731344Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 731344
[F:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][NH:7][C@H:8]2[CH2:12][CH2:11][CH2:10][C@H:9]2[C:13]([O:15]C)=O)=[CH:4][CH:3]=1.[I:19][C:20]1[CH:35]=[CH:34][C:23]2[NH:24][C:25]([CH2:30][C:31](O)=[O:32])=[N:26][S:27](=[O:29])(=[O:28])[C:22]=2[CH:21]=1.CN1CCOCC1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C@@H:8]3[C@@H:9]([CH2:10][CH2:11][CH2:12]3)[C:13]([OH:15])=[C:30]([C:25]3[NH:24][C:23]4[CH:34]=[CH:35][C:20]([I:19])=[CH:21][C:22]=4[S:27](=[O:28])(=[O:29])[N:26]=3)[C:31]2=[O:32])=[CH:17][CH:18]=1

Komponenten

7

Edukt 4

HCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57832628methyl (1R,2S)-2-(4-fluoro-benzylamino)-cyclopentanecarboxylateHCID 59853574(7-Iodo-1,1-dioxo-1,4-dihydro-1lambda6-benzo[1,2,4]thiadiazin-3-yl)-acetic acid

Produkt 1

HCID 135955738(4aR,7aS)-1-[(4-fluorophenyl)methyl]-4-hydroxy-3-(7-iodo-1,1-dioxo-4H-1$l^{6},2,4-benzothiadiazin-3-yl)-5,6,7,7a-tetrahydro-4aH-cyclopenta[b]pyridin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a stirred solution of methyl (1R,2S)-2-(4-fluoro-benzylamino)-cyclopentanecarboxylate (2.50 g, 10 mmol) in anhydrous N,N-dimethylformamide (25 mL) under a nitrogen atmosphere, (7-iodo-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-3-yl)-acetic acid (prepared as described in Example 24b, 3.66 g, 10 mmol), N-methylmorpholine (2.20 mL, 20 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.92 g, 10 mmol) were added sequentially. After stirring at 25° C. for 16 h, the reaction mixture was diluted with ethyl acetate, washed with a 1.0 M aqueous hydrochloric acid solution and saturated aqueous brine solution, dried over sodium sulfate and filtered. The filtrate was concentrated in vacuo to afford the crude amide intermediate.

Aufarbeitung

  1. washwashed with a 1.0 M aqueous hydrochloric acid solution and saturated aqueous brine solution
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-bb830a6631cf4519b24ca2aa91b30bfe
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07582626B2

Notizen zur Reaktion

Wird geladen…